Sodium Hydroxide → 4-(3-Hydroxymethyl-[1,2,4]triazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 80636노트

반응식

HRID 80636 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[N:17][C:16]([C:19](OCC)=[O:20])=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:18]=[N:17][C:16]([CH2:19][OH:20])=[N:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 687480884-(3-Ethoxycarbonyl-[1,2,4]triazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 577083924-(3-Hydroxymethyl-[1,2,4]triazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 4-(3-ethoxycarbonyl-[1,2,4]triazol-1-yl) -piperidine-1-carboxylic acid tert-butyl ester (from Step 1, 0.64 g, 2.06 mmol) in THF (10 mL) at 0° C. was added lithium aluminum hydride (0.078 g, 2.06 mmol). The solution was allowed to warm to room temperature and stirred for 4 hours. The solution was diluted with THF, cooled to 0° C., and 1 mL of water was added followed by 1 mL of 15% NaOH and 3 mL of water. The solution was allowed to warm to room temperature and stirred for 15 minutes. MgSO4 was then added and the solution was stirred an additional 15 minutes, filtered and concentrated in vacuo. The residue was purified by flash chromatograph on silica gel with MeOH and CH2Cl2 to afford the desired product. 1H NMR (CDCl3): δ 8.03 (1H, s), 4.79 (2H, d), 4.25 (3H, m), 2.95 (2H, m), 2.58 (1H, t), 2.19 (2H, m), 1.98 (2H, m), 1.43 (9H, s).

후처리

  1. temperaturecooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for 15 minutes
  4. stirringthe solution was stirred an additional 15 minutes
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatograph on silica gel with MeOH and CH2Cl2

출처 및 근거

ORD 기록
ord-5210f1780cd0423aa7dfe677118ae21f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846675B2

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